33261-95-9

Basic information

• Product Name: (17beta)-3,3-[ethylenebis(oxy)]-17-hydroxyandrost-5-ene-17-carbonitrile
• Synonyms: (17beta)-3,3-[ethylenebis(oxy)]-17-hydroxyandrost-5-ene-17-carbonitrile;17-Hydroxyspiro[androstane-3,2'-[1,3]dioxolan]-5-ene-17β-carbonitrile
• CAS NO: 33261-95-9
• Molecular Formula: C₂₂H₃₁NO₃
• Molecular Weight: 357.48644
• EINECS: 251-433-9
• Mol File: 33261-95-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 519.2°Cat760mmHg
• Flash Point: 267.8°C
• Appearance: /
• Density: 1.2g/cm³
• CAS DataBase Reference: (17beta)-3,3-[ethylenebis(oxy)]-17-hydroxyandrost-5-ene-17-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (17beta)-3,3-[ethylenebis(oxy)]-17-hydroxyandrost-5-ene-17-carbonitrile(33261-95-9)
• EPA Substance Registry System: (17beta)-3,3-[ethylenebis(oxy)]-17-hydroxyandrost-5-ene-17-carbonitrile(33261-95-9)

Safety Data

• Hazardous Substances Data: 33261-95-9(Hazardous Substances Data)

Usage

General Description

(17beta)-3,3-[ethylenebis(oxy)]-17-hydroxyandrost-5-ene-17-carbonitrile, also known as ethinylestradiol, is a synthetic derivative of the hormone estrogen. It is commonly used as a component in hormonal contraceptives and hormone replacement therapy for menopausal symptoms. Ethinylestradiol works by mimicking the effects of natural estrogen in the body, helping to regulate the menstrual cycle and prevent ovulation. It is also used in the treatment of conditions such as acne and certain types of breast cancer. However,

Upstream product

• 975-57-5 3,3-(ethylenedioxy)-5-androsten-17β-ol 
• 6173-28-0 17β-acetoxy-3,3-ethanediyldioxy-androst-5-ene 
• 151-50-8 potassium cyanide 
• 3754-63-0 3,3-ethylenedioxy-5-androsten-17-one 
• 111-46-6 diethylene glycol 

Relevant articles and documents

Synthesis and characterization by 1H and 13C nuclear magnetic resonance spectroscopy of 17 alpha-cyano, 17 alpha-aminomethyl, and 17 alpha-alkylamidomethyl derivatives of 5 alpha-dihydrotestosterone and testosterone.

17 alpha-Aminomethyl, 17 alpha-acetamidomethyl, and 17 alpha-hemiglutaramidomethyl derivatives of dihydrotestosterone and testosterone have been prepared by hydrocyanation of 3,3'-(ethylenedioxy)-5 alpha-androstan-17-one and 3,3'-ethylenedioxyandrost-5-en-17-one, reduction of the corresponding acetylated 17 alpha-cyanohydrins with lithium aluminium hydride, and acylation of the resulting 17 alpha-aminomethyl derivatives with either acetic anhydride or the mono acid chloride of glutaric acid mono methyl ester. Saponification of the 17 alpha-hemiglutaramidomethyl methyl esters gave the corresponding hemiglutaramido derivatives, while acid hydrolysis of the 3-ethylene ketal group of 17 alpha-acetamidomethyl and 17 alpha-hemiglutaramidomethyl derivatives regenerated the 3-oxo and 3-oxo-4-ene functions. The 17 alpha-configuration of 17-substituted steroids was determined by 1H and 13C NMR and confirmed by comparing with NMR data for 17 alpha- and 17 beta-cyano-17-hydroxyandrost-4-en-3-one, 17 beta-cyano-3,3'-(ethylenedioxy)androst-5-en-17-ol, 17 alpha-alkynyl, and 17 alpha-hexanoic derivatives of dihydrotestosterone and testosterone, of known 17-configurations. Several ambiguous assignments of 13C NMR signals of 17 alpha-substituted steroids and unsubstituted 17 beta-hydroxy or 17-oxo precursors have been resolved using steroid analogs deuterated at positions C5-7, or C16 for androstane derivatives, and at positions C6-7, or C7 for androstene derivatives. 17 alpha-Aminomethyl and 17 alpha-alkylamidomethyl derivatives of dihydrotestosterone and testosterone are useful intermediates for the access to potential ligands of androgen-binding proteins necessary for affinity chromatography purification or affinity-labeling experiments.